Cyclohexanone → 1-[1-(Piperidin-1-yl)cyclohexyl]methanamine

HRID 1283530Notes

Reaction equation

HRID 1283530 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C-:8]#[N:9].[K+].[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>O.C(O)C>[NH2:9][CH2:8][C:11]1([N:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 9032Potassium CyanideHCID 2723721Piperidine, hydrochloride (1:1)

Product 1

HCID 3984021-[1-(Piperidin-1-yl)cyclohexyl]methanamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Piperidine hydrochloride (24.1 g. 0.2 mole) and KCN (13.0 g. 0.2 mole) were dissolved in water (80 ml) and ethanol (160 ml). To this stirred solution was added dropwise a solution of cyclohexanone (19.6 g., 0.2 mole) in ethanol (40 ml), the mixture refluxed for 24 hr. Ethanol was then removed under reduced pressure and the residue extracted with chlorofrom. The extract was washed with water, dried (Na2SO4) and evaporated under reduced pressure to give a pale, amber oil (27.0 g. 68.8%) which crystallized on standing. Recrystallization from ethanol afforded colourless plates of 1-(1-cyanocyclohexyl)piperidine m.p. 67°-8°.

Workup

  1. temperaturethe mixture refluxed for 24 hr
  2. customEthanol was then removed under reduced pressure
  3. extractionthe residue extracted with chlorofrom
  4. washThe extract was washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customto give a pale, amber oil (27.0 g. 68.8%) which
  8. customcrystallized
  9. customRecrystallization from ethanol afforded colourless plates of 1-(1-cyanocyclohexyl)piperidine m.p. 67°-8°

Sources & evidence

ORD record
ord-4fb16c7c5b6b48adb1df837ab7ee73ab
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

Loading…